Bobby Kennedy is a decorated former law-enforcement officer (American Police Hall of Fame Silver Star for Bravery and Legion of Honor "Purple Heart") He is the third son in a four son law enforcement family. His oldest brother is retired as a sworn officer and now owns a Private Investigations business. Another older brother is a Sargeant with the Wilmington North Carolina Police Dept. (WPD), and his younger brother is a Special Agent with the North Carolina State Bureau of Investigations (NCSBI). Bobby's time in law-enforcement included deep cover operations as well as investigations and patrol.

He was a single parent of his oldest son Bobby Gene Kennedy, Jr. for 6 years and then he married Sherry "Nikki" Barwick. He and Nikki then had Bobby Austin, Bobbie Nicole, and are now expecting one more Bobby or Bobbie.

In 2004 at the age of 37, Bobby suffered 2 massive heart attacks and had to undergo open-heart surgery. After recovering from the surgery Nikki informed Bobby that his days of chasing "bad guys" were over and he would have to find a new line of work. He has played a police officer on seasons 3 and 4 of "One Tree Hill" and has appeared at GoodNight's Comedy Club in Raleigh, N.C.

Most of Bobby's humor is stories about his life. Everything about his life ( his career as an officer, his marriage at the age of 33 to Nikki who was 18, his unplanned fourth time father-to-be status at the age of 40, and even his heart attacks) has a story.